Indole → HCID 9942622, compound

HRID 1883456Notes

Reaction equation

HRID 1883456 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:19]1[CH:20]=[C:21]([CH3:26])[CH:22]=[C:23]([CH3:25])[CH:24]=1.[OH-].[NH4+].CCCCCCCCCCCC>[Cu]I.C(N(CC)C(=O)C1C(=CC=CC=1)O)C.O.C(OCC)(=O)C>[CH3:26][C:21]1[CH:20]=[C:19]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:24]=[C:23]([CH3:25])[CH:22]=1

Participants

10

Reactant 5

HCID 798IndoleHCID 8182DodecaneHCID 14923Ammonium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 9942622HCID 9942622, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 88006DiethylsalicylamideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

CuI (10 mg, 0.05 mmol), N,N-diethylsalicylamide (10 mg, 0.05 mmol), indole (176 mg, 1.5 mmol) and K3PO4 (425 mg, 2.0 mmol) were put into a screw-capped test tube with a Teflon-lined septum. The tube was then evacuated and backfilled with argon (3 cycles). 5-Bromo-m-xylene (136 μL, 1.0 mmol) was added by a syringe. The reaction mixture was stirred at 100° C. for 20 h. The reaction mixture was allowed to reach room temperature. Ethyl acetate (˜2 mL), water (˜10 mL), ammonium hydroxide (˜0.5 mL) and dodecane (227 μL) were added. The organic phase was analyzed by GC or GC-MS. The reaction mixture was further extracted by ethyl acetate (4×10 mL). The combined organic phases were washed with brine and dried over Na2SO4. Solvent was removed in vacuo and the yellow residue was purified by column chromatography on silica gel using hexane/ethyl acetate (10:1) as eluent to afford the desired product as a brown solid (196 mg, 89% yield).

Workup

  1. customThe tube was then evacuated
  2. customto reach room temperature
  3. extractionThe reaction mixture was further extracted by ethyl acetate (4×10 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. customSolvent was removed in vacuo
  7. customthe yellow residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7582471e1aca4709a2968f042330ec1f
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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